SmtpClientDiag

1.2.0.0

Test-SmtpSaslAuthBlob.psm1

                                <#

 .Synopsis

  Diagnostic module for SMTP Sasl Auth Blob

 .Description

  Utility module for testing SMTP Sasl Auth Blob for common issues and misconfigurations.

 .Parameter EncodedAuthBlob

  Base64 encoded auth blob to test.

 .Example

   # Test an auth blob

   Test-SmtpSaslAuthBlob -EncodedAuthBlob 'dXNlcj1zb21ldXNlckBleGFtcGxlLmNvbQFhdXRoPUJlYXJlciB5YTI5LnZGOWRmdDRxbVRjMk52YjNSbGNrQmhkSFJoZG1semRHRXVZMjl0Q2cBAQ==' -Verbose

    AuthBlobUserName        : someuser@example.com

    AuthBlobToken           : dXNlcj1zb21ldXNlckBleGFtcGxlLmNvbQFhdXRoPUJlYXJlciB5YTI5LnZGOWRmdDRxbVRjMk52YjNSbGNrQmhkSFJoZG1semRHRXVZMjl0Q2cBAQ==

    OAuthTokenAudience      : https://outlook.office.com

    OAuthTokenScopes        : SMTP.Send

    OAuthTokenRoles         :

    OAuthTokenUpn           : someuser@example.com

    OAuthTokenExpirationUtc : 01/01/1970 12:00:00 AM

    ApplicationId           : 9954180a-16f4-4683-aaaaaaaaaaaa

    AppDisplayName          : My OAuth SMTP Application

    IsAuthBlobValid         : True

    IsAuthTokenValid        : True

#>

function Test-SmtpSaslAuthBlob() {

    [CmdletBinding()]

    param(

        [Parameter(Mandatory = $false, Position = 0)]

        [string]$EncodedAuthBlob

    )

    $Script:BlobResult = [PSCustomObject] @{

        AuthBlobUserName        = $null

        AuthBlobToken           = $null

        OAuthTokenAudience      = $null

        OAuthTokenScopes        = $null

        OAuthTokenRoles         = $null

        OAuthTokenUpn           = $null

        OAuthTokenExpirationUtc = $null

        ApplicationId           = $null

        AppDisplayName          = $null

        IsAuthBlobValid         = $false

        IsAuthTokenValid        = $false

    }

    # Write error if no auth blob is provided instead of making parameter mandatory.

    # Making it mandatory would truncate the string if user provided after execution

    if ([string]::IsNullOrEmpty($EncodedAuthBlob)) {

        Write-Error "AuthBlob is null or empty. Please supply a value to test." -ErrorAction Stop

    }

    $decodedAuthBlob = $null

    try {

        $decodedAuthBlob = DecodeBase64Value($EncodedAuthBlob)

    }

    catch {

        Write-Verbose "Failed to decode auth blob: $EncodedAuthBlob"

        Write-Error "AuthBlob is not valid base64 encoded string. Check your input and try again." -ErrorAction Stop

    }

    [char[]]$charArray = $decodedAuthBlob.ToCharArray()

    [int]$userIndex = $decodedAuthBlob.IndexOf("user=")

    [int]$authIndex = $decodedAuthBlob.IndexOf("auth=")

    [int]$bearerIndex = $decodedAuthBlob.IndexOf("Bearer ")

    [char]$ctrlA = [char]0x01

    # Validate that auth blob is correctly formatted

    # Example: base64("user=" + userName + "^Aauth=Bearer " + accessToken + "^A^A")

    # ^A represents a Control + A (%x01) character

    # Check if 'user' is present at the beginning of the string

    if ($userIndex -ne 0) {

        Write-Verbose "Invalid Authblob. Expected 'user' at index 0. IndexOf('user='):$userIndex"

        Write-Error "Authblob is incorrectly formatted. User not found." -ErrorAction Stop

    }

    # Check if 'auth' is present after 'user'

    if ($authIndex -eq -1) {

        Write-Verbose "Invalid Authblob. 'auth' not found in auth blob."

        Write-Error "Authblob is incorrectly formatted. Auth not found." -ErrorAction Stop

    }

    # Check if 'Bearer' is present after 'auth'

    if ($bearerIndex -eq -1 -or $bearerIndex -lt $authIndex) {

        Write-Verbose "Invalid Authblob. 'Bearer' not found in auth blob or not in correct position. IndexOf('Bearer '):$bearerIndex"

        Write-Error "Authblob is incorrectly formatted. Bearer not found." -ErrorAction Stop

    }

    # Check if CTRL-A character is present before auth

    if ($charArray[$authIndex - 1] -ne $ctrlA) {

        $Script:BlobResult | Format-List

        $charHex = GetCharHexValue($charArray[$authIndex - 2])

        Write-Verbose "Invalid Authblob. Expected ascii character 0x01 before 'auth' but found char '0x$charHex' at index '$authIndex'."

        Write-Error "Authblob is incorreclty formatted. Missing CTRL-A character." -ErrorAction Stop

    }

    # Check if CTRL-A is present at the end of the string

    if ($charArray[-1] -ne $ctrlA -and $charArray[-2] -ne $ctrlA) {

        $Script:BlobResult | Format-List

        Write-Verbose "Invalid Authblob. Expected ascii character 0x01 0x01 at end of string but found '$($charArray[-1])$($charArray[-2])'."

        Write-Error "Authblob is incorreclty formatted. Missing CTRL-A character." -ErrorAction Stop

    }

    $Script:BlobResult.AuthBlobUserName = $decodedAuthBlob.Substring($userIndex + 5, $authIndex - 6)

    $Script:BlobResult.AuthBlobToken = $decodedAuthBlob.Substring($authIndex + 5, $decodedAuthBlob.Length - $authIndex - 7).Replace("Bearer ", "")

    if ([string]::IsNullOrEmpty($Script:BlobResult.AuthBlobUserName)) {

        $Script:BlobResult | Format-List

        Write-Verbose "Found 'user' in auth blob but it contains no value."

        Write-Error "AuthBlob does not contain a user" -ErrorAction Stop

    }

    if ([string]::IsNullOrEmpty($Script:BlobResult.AuthBlobToken)) {

        $Script:BlobResult | Format-List

        Write-Verbose "Found 'auth' in auth blob but it contains no value."

        Write-Error "AuthBlob does not contain a token" -ErrorAction Stop

    }

    try {

        CheckAccessToken($Script:BlobResult.AuthBlobToken)

    }

    catch {

        $Script:BlobResult | Format-List

        Write-Error $_.Exception

        Write-Error "Token in auth blob is invalid." -ErrorAction Stop

    }

    # If we get here, we're good

    $Script:BlobResult.IsAuthBlobValid = $true

    return $Script:BlobResult

}

function CheckAccessToken($encodedToken) {

    if ([string]::IsNullOrEmpty($encodedToken)) {

        Write-Verbose "Token is null or empty. Skipping token verfication."

        $Script:BlobResult.IsAuthTokenValid = $false

        return

    }

    [bool]$tokenValid = $true

    [string]$decodedToken = $null

    [object]$token = $null

    [bool]$isAppAuth = $false

    [string[]]$tokenParts = $encodedToken.Split(".")

    # Token should have header, payload and signature

    if ($tokenParts.Count -ne 3 -or [string]::IsNullOrEmpty($tokenParts[0]) -or [string]::IsNullOrEmpty($tokenParts[1])) {

        throw "Invalid token. Token header or payload is null or empty."

    }

    # Can header and payload be decoded? Throws exception if not

    try {

        DecodeBase64Value($tokenParts[0]) | Out-Null

        $decodedToken = DecodeBase64Value($tokenParts[1])

        $token = ConvertFrom-Json $decodedToken

    }

    catch {

        throw "Failed to decode authentication token or token is not valid JSON."

    }

    $Script:BlobResult.OAuthTokenAudience = $token.aud

    $Script:BlobResult.OAuthTokenUpn = $token.upn

    $Script:BlobResult.OAuthTokenScopes = $token.scp

    $Script:BlobResult.OAuthTokenRoles = $token.roles

    $Script:BlobResult.OAuthTokenExpirationUtc = [System.DateTimeOffSet]::FromUnixTimeSeconds($token.exp).UtcDateTime

    $Script:BlobResult.ApplicationId = $token.appid

    $Script:BlobResult.AppDisplayName = $token.app_displayname

    if (-not [string]::IsNullOrEmpty($token)) {

        # Check for correct audience claim

        if ($token.aud -ne "https://outlook.office365.com" -and $token.aud -ne "https://outlook.office.com") {

            $tokenValid = $false

            Write-Verbose "Unexpected audience claim. Expected 'https://outlook.office365.com' or 'https://outlook.office.com' but found '$($token.aud)'."

            Write-Warning "Authentication token contains an invalid audience claim for SMTP Client Submission."

        }

        # Likely client credential flow if UPN claim is null or empty

        if ([string]::IsNullOrEmpty($token.upn)) {

            $isAppAuth = $true

            Write-Verbose "UPN claim is null or empty."

            Write-Warning "Application authentication detected. UPN claim not found in token."

        }

        # If delegated permission check if upn in token matches username in auth blob

        # Token can be valid but must be for the same user as the auth blob

        if (-not $isAppAuth) {

            if ($token.upn -ne $Script:BlobResult.AuthBlobUserName) {

                $tokenValid = $false

                Write-Verbose "UPN claim in token does not match username in auth blob. UPN claim:'$($token.upn)' Username:'$($Script:BlobResult.AuthBlobUserName)'."

                Write-Warning "UPN in authentication token and AuthBlob do not match."

            }

        }

        # If using client credential flow check the roles claim

        if ($isAppAuth) {

            Write-Verbose "Checking roles claim for SMTP.SendAsApp permission."

            $permissions = $token.roles.Split()

            if (-not $permissions.Contains("SMTP.SendAsApp")) {

                $tokenValid = $false

                Write-Verbose "Not checking scopes claim as this is not user authentication."

                Write-Verbose "Invalid roles in token. Expected 'SMTP.SendAsApp' but found '$($token.roles)'."

                Write-Warning "Required permission for SMTP Client Submission not found in token."

            }

        }

        # Else check the scopes claim

        else {

            Write-Verbose "Not checking roles claim as this is not application authentication."

            Write-Verbose "Checking scopes claim for SMTP.Send permission."

            $permissions = $token.scp.Split()

            if (-not $permissions.Contains("SMTP.Send")) {

                $tokenValid = $false

                Write-Verbose "Invalid scope in token. Expected 'SMTP.Send' but found '$($token.scp)'."

                Write-Warning "Required permission for SMTP Client Submission not found in token."

            }

        }

        # Check if token is expired

        $currentDateTime = Get-Date

        if ($currentDateTime.ToUniversalTime() -gt $Script:BlobResult.OAuthTokenExpirationUtc) {

            $tokenValid = $false

            Write-Verbose "Token has expired. Token expiration date: '$tokenExpiration'. Current date: '$currentDateTime'."

            Write-Warning "Authentication token has expired."

        }

    }

    else {

        $tokenValid = $false

    }

    $Script:BlobResult.IsAuthTokenValid = $tokenValid

}

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